Polyoxyalkylene polyamines are well known. Typically, they may be used as curing agents for epoxy resins, as cross-linking agents or binders for textiles, and as intermediates in the preparation of polyureas, including flexible urethane foams and urethane elastomers.
A. V. Pocius in "Elastomer Modification of Structural Adhesives," Rubber Chemistry and Technology, Vol. 58, No. 3, July-August, 1985, pp. 622-635 presents a survey of some of the various elastomers used in providing structural adhesives with excellent shear strength and substantial resistance to cleavage. Some of these elastomers contain butadiene.
A number of patents are known to disclose polyoxyalkylene polyamines and methods for making them. For example, U.S. Pat. No. 3,236,895 teaches polyoxyalkylene-polyamines that are predominately diamines of the generic formula: ##STR1## wherein each R represents an independently selected radical from the group consisting of hydrogen and lower alkyl radicals having from 1 to 6 carbon atoms and whereiin a represents an integer from 1 to 30. A method for making epoxy resins by admixing a polyglycidyl ether of a phenolic compound and a polyoxyalkylenepolyamine of U.S. Pat. No. 3,236,895, as a curing agent, is set out in U.S. Pat. No. 3,462,393. Also related to polyamines are U.S. Pat. Nos. 4,124,758, covering aminated cellulose derivatives prepared by the reductive amination of a hydroxyl cellulose; 4,139,698 covering aminated starch derivatives prepared by the reductive amination of an oxidized starch by reaction with ammonia or ammonium hydroxide; 4,181,682 covering polymeric amines of the formula: ##STR2## where x ranges from 6 to 50, y and z range from 1 to 20 with the sum of y and z being from 6 to 40; and 4,618,717 covering a process for the conversion of oxyethylene glycol monoalkyl ethers to the corresponding primary amines by reaction with ammonia in the presence of a nickel-copper-chromium-containing catalyst. U.S. Pat. No. 3,654,370 discloses that polyoxyalkylene polyamines may be prepared by treating the corresponding polyoxyalkylene polyols with ammonia and hydrogen over a catalyst prepared by the reduction of a mixture of the oxides of nickel, copper and chromium. The polyoxyalkylene polyols may be obtained by the addition of one or more alkylene oxides to an aliphatic polyhydric alcohol.
Room-temperature-curable compositions can be prepared readily by mixing (a) 100 parts by weight (pbw) of at least one non-cycloaliphatic epoxy resin and (b) from about 1 to about 1,000 pbw of at least one amine-terminated liquid polymer having a carbon-carbon backbone, (c) optionally, a chain extender or cross-linker and (d) a curing agent, according to U.S. Pat. No. 4,129,670. In this patent, the amine-terminated liquid polymers have the formula Y--(CO)--(B)--(CO)--Y, where Y is a univalent radical obtained by removing hydrogen from an amine group of an aliphatic, alicyclic, heterocyclic or aromatic amine containing at least two primary and/or secondary amine groups, and B is a polymeric backbone comprising carbon-carbon linkages. Polybutadiene is present in the long list of apparently suitable polymeric backbones recited therein. Another patent of interest is U.S. Pat. No. 4,521,581 which describes a process for the making of polymer polyols where a relatively low molecular weight liquid polymer of an ethylenically unsaturated monomer is mixed with a polyol and crosslinked in the polyol. The relatively low molecular weight polymer which is mixed in the polyol may have a variety of microstructures since the low molecular weight polymer is prepared separately from the polyol. Butadiene is recited in a long list of suitable unsaturated monomers.
It is always desirable to produce polyamines with improved properties, such as being able to impart greater water resistance to the resulting epoxy resin.